Along with an increase in number of pharmaceuticals, agricultural chemicals, and liquid crystal materials containing compounds each having an asymmetric carbon, the need for accurately determining the optical purity of each of those compounds and their synthesis intermediates has been arising. NMR involving the utilization of a chiral derivatizing reagent or a chiral shift reagent (or a chiral solvation reagent), high performance liquid chromatography (HPLC) and gas chromatography, each involving the use of a chiral column packed with a chiral stationary phase, have each been known as a method of determining the optical purity.
Of those, the HPLC has been widely acknowledged as a method showing highly reliable results of analysis for a wide range of compounds. Moreover, the HPLC has the following characteristic. That is, the method enables the fractionation of chiral compounds as well as the analysis of the compounds. A stationary phase formed of a carrier such as a silica gel and a chiral selector supported by being covalently bonded to the carrier has been generally known as the chiral stationary phase used in the HPLC. For example, a stationary phase obtained by covalently bonding a cyclic amide compound to a silica gel as a carrier has been known as such chiral stationary phase (see, for example, Non-patent Documents 1 and 2).
Meanwhile, for example, a cyclic amide compound having an ability to function as a chiral shift reagent capable of asymmetry recognition by an NMR spectrum has been reported as the chiral shift reagent used in the NMR (see, for example, Non-patent Document 3). However, with particular regard to a compound having an ability to function as a chiral shift reagent, it has been known that a recognition ability is exerted only in an aprotic solvent such as deuterated chloroform and that causing a protic deuterated solvent such as an alcohol to coexist reduces the recognition ability. Meanwhile, assorted solvents including an alcohol are each used as a moving phase for a recognition agent for chromatography. Accordingly, it cannot be expected that the very asymmetry recognition ability of the compound having an ability to function as a chiral shift reagent is exerted, and investigations on the exertion have hardly been conducted.    Non-patent Document 1: D. W. Armstrong, Y. Tang, S. Chen, Y. Zhou, C. Bagwill, J.-R. Chen, Macrocyclic antibiotics as a new class of chiral selectors for liquid chromatography. Anal. Chem., 66(9), 1473-1484 (1994).    Non-patent Document 2: F. Gasparrini, D. Misiti, M. Pierini, C. Villani, A chiral A2B2 macrocyclic minireceptor with extreme enantioselectivity. Org. Lett., 4(23), 3993-3996 (2002).    Non-patent Document 3: T. Ema, D. Tanida, T. Sakai, Versatile and practical macrocyclic reagent with multiple hydrogen-bonding sites for chiral discrimination in NMR. J. Am. Chem. Soc., 129(34), 10591-10596 (2007).